JP2022183109A - Host materials, organic electroluminescent compound, and organic electroluminescent device including the same - Google Patents

Abstract

To provide a plurality of host materials, an organic electroluminescent compound, and an organic electroluminescent device including the same.SOLUTION: The present disclosure relates to a plurality of host materials, an organic electroluminescent compound, and an organic electroluminescent device including the same. It is possible to manufacture an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or life property than conventional organic electroluminescent devices by including the organic electroluminescent compound, or by including a predetermined combination of compounds in the present disclosure as a plurality of host materials.SELECTED DRAWING: Figure 1

Description

The present disclosure relates to multiple host materials, organic electroluminescent compounds, and organic electroluminescent devices containing the same.

Small molecule green organic electroluminescent devices (OLEDs) were first developed by Tang et al. of Eastman Kodak in 1987 by using a TPD/ALq3 bilayer consisting of a light emitting layer and a charge transport layer. Since then, the development of OLEDs has been achieved rapidly and OLEDs have been commercialized. At present, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel mounting. However, in many applications such as TV and lighting, the lifetime of OLEDs is insufficient and higher efficiencies of OLEDs are still needed. Typically, the higher the brightness of an OLED, the shorter the lifetime it has. Therefore, OLEDs with high luminous efficiency and/or long lifetime characteristics are required for long-term use and high resolution of displays.

Various materials or concepts have been proposed for the organic layers of OLEDs to enhance the luminous efficiency, driving voltage and/or lifetime. However, they were not satisfactory in practice.

In the meantime, US Pat. Nos. 5,301,000, 5,500,000 and 5,000,009 disclose multiple host materials including dibenzofuran or dibenzothiophene derivatives and biscarbazole derivatives. However, the aforementioned references do not specifically disclose the particular combination of host materials claimed in this disclosure, particularly multiple host materials including the deuterium-substituted second host material. In addition, developing luminescent materials with improved performance, e.g., improved drive voltage, luminous efficiency, power efficiency and/or lifetime characteristics compared to previously disclosed combinations of specific compounds , is in constant demand.

U.S. Pat. No. 9,397,307 Korean Patent Application Publication No. 2018-0038834 Korean Patent No. 1885898

It is an object of the present disclosure to provide multiple host materials that can provide organic electroluminescent devices with improved driving voltage, luminous efficiency and/or lifetime characteristics. Another object of the present disclosure is to provide organic electroluminescent compounds suitable for application in organic electroluminescent devices. Yet another object of the present disclosure is an organic electroluminescent material having improved driving voltage, luminous efficiency and/or lifetime characteristics by including a specific compound as a host material or by including a specific combination of compounds. to provide the device.

As a result of intensive research to solve the technical problem, the present inventors have achieved the above object by providing a first host material comprising a compound represented by the following formula 1 and a compound represented by the following formula 2 We have found that this can be achieved with a plurality of host materials, including a second host material comprising a compound. In addition, the present inventors have found that the above object can be achieved by an organic electroluminescent compound represented by the following formula 1-A or 1-B.

式１において、
Ｘは、Ｏ、Ｓ又はＳｅを表し；
ＨＡｒは、少なくとも１個の窒素原子を含有する置換若しくは非置換（３～３０員）ヘテロアリールを表し；
Ｌは、単結合、置換若しくは非置換（Ｃ６～Ｃ３０）アリーレン、又は置換若しくは非置換（３～３０員）ヘテロアリーレンを表し：
Ｒ_１及びＲ_２は、それぞれ独立して、水素、重水素、置換若しくは非置換（Ｃ６～Ｃ３０）アリール、置換若しくは非置換（３～３０員）ヘテロアリール、又は－ＳｉＲ_１１Ｒ_１２Ｒ_１３を表し；
Ｒ_１１～Ｒ_１３は、それぞれ独立して、置換若しくは非置換（Ｃ１～Ｃ３０）アルキル、置換若しくは非置換（Ｃ６～Ｃ３０）アリール、又は置換若しくは非置換（３～３０員）ヘテロアリールを表し；
ａは１～４の整数を表し、ｂは１～３の整数を表し、ここで、ａ及びｂのそれぞれが２以上の整数である場合、Ｒ_１のそれぞれ及びＲ_２のそれぞれは、同じものであっても又は異なってもよい。

In formula 1,
X represents O, S or Se;
HAr represents substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen atom;
L represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene:
R ₁ and R ₂ each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or —SiR ₁₁ R ₁₂ R ₁₃ represent;
R ₁₁ to R ₁₃ each independently represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
a represents an integer of 1 to 4, b represents an integer of 1 to 3, wherein when each of a and b is an integer of 2 or more, each of R ₁ and each of R ₂ are the same or may be different.

式２において、
Ａ_１及びＡ_２は、それぞれ独立して、置換若しくは非置換（Ｃ６～Ｃ３０）アリール、置換若しくは非置換ジベンゾフラニル、置換若しくは非置換ジベンゾチオフェニル、又は置換若しくは非置換カルバゾリルを表し；
Ｘ_１１～Ｘ_２６は、それぞれ独立して、水素、重水素、置換若しくは非置換（Ｃ６～Ｃ３０）アリール、又は置換若しくは非置換（３～３０員）ヘテロアリールを表し；
Ｘ_１５～Ｘ_１８の１つ及びＸ_１９～Ｘ_２２の１つは、互いに結合して単結合を形成しており；
但し、Ｘ_１１、Ｘ_１８、Ｘ_１９及びＸ_２６の少なくとも１つは、重水素であることを条件とする。

In formula 2,
A ₁ and A ₂ each independently represent substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;
X ₁₁ to X ₂₆ each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;
one of X ₁₅ to X ₁₈ and one of X ₁₉ to X ₂₂ are bonded to each other to form a single bond;
provided that at least one of X ₁₁ , X ₁₈ , X ₁₉ and X ₂₆ is deuterium.

式１－Ａにおいて、
Ｘ_ａは、Ｏ又はＳを表し；
Ｒ_４１～Ｒ_４８は、それぞれ独立して、水素、重水素、又は非置換の若しくは重水素、（Ｃ１～Ｃ６）アルキル及び（Ｃ６～Ｃ１８）アリールの少なくとも１つで置換された（Ｃ６～Ｃ１８）アリールを表すか、又は以下の式１－ａで表され、但し、Ｒ_４１～Ｒ_４８の少なくとも１つは、以下の式１－ａ：

［式１－ａ中、
Ｒａ～Ｒｄは、それぞれ独立して、水素、重水素、又は非置換の若しくは重水素、（Ｃ１～Ｃ６）アルキル及び（Ｃ６～Ｃ１８）アリールの少なくとも１つで置換された（Ｃ６～Ｃ１８）アリールを表し；
Ａｒ_ａ及びＡｒ_ｂは、それぞれ独立して、非置換の若しくは重水素で置換されたフェニル、非置換の若しくは重水素で置換されたナフチル、非置換の若しくは重水素で置換されたビフェニル、非置換の若しくは重水素で置換されたテルフェニル、非置換の若しくは重水素で置換されたカルバゾリル、非置換の若しくは重水素で置換されたジベンゾフラニル、非置換の若しくは重水素で置換されたジベンゾチオフェニル、又はそれらの組合せを表し、但し、Ａｒ_ａ及びＡｒ_ｂの少なくとも１つは、置換若しくは非置換カルバゾリルを含むことを条件とする］
で表されることを条件とする。

In formula 1-A,
X _a represents O or S;
R ₄₁ to R ₄₈ are each independently hydrogen, deuterium, or unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl (C6-C18 ) aryl or represented by formula 1-a below, provided that at least one of R ₄₁ to R ₄₈ is represented by formula 1-a below:

[In formula 1-a,
Ra-Rd are each independently hydrogen, deuterium, or (C6-C18)aryl unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl represents;
Ar _a and Ar _b are each independently unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterated terphenyl, unsubstituted or deuterated carbazolyl, unsubstituted or deuterated dibenzofuranyl, unsubstituted or deuterated dibenzothiophenyl or combinations thereof, with the proviso that at least one of Ar _a and Ar _b comprises a substituted or unsubstituted carbazolyl]
is expressed as a condition.

式１－Ｂにおいて、
Ｘ_ａは、Ｏ又はＳを表し；
Ｒ_４１～Ｒ_４８は、それぞれ独立して、水素、重水素、又は非置換の若しくは重水素、（Ｃ１～Ｃ６）アルキル及び（Ｃ６～Ｃ１８）アリールの少なくとも１つで置換された（Ｃ６～Ｃ１８）アリール、或いは－Ｌ_ｂ－ＨＡｒ_ｂを表し、但し、Ｒ_４１～Ｒ_４８の少なくとも１つは、－Ｌ_ｂ－ＨＡｒ_ｂを表し；
Ｌ_ｂは、非置換の若しくは重水素で置換されたナフタレンを表し；
ＨＡｒ_ｂは、以下の式１－ｂ：

［式１－ｂ中、
Ａｒ_ａ及びＡｒ_ｂは、それぞれ独立して、非置換の若しくは重水素で置換されたフェニル、非置換の若しくは重水素で置換されたナフチル、非置換の若しくは重水素で置換されたビフェニル、非置換の若しくは重水素で置換されたテルフェニル、非置換の若しくは重水素で置換されたカルバゾリル、非置換の若しくは重水素で置換されたジベンゾフラニル、非置換の若しくは重水素で置換されたジベンゾチオフェニル、又はそれらの組合せを表し、但し、Ａｒ_ａ及びＡｒ_ｂの少なくとも１つは、非置換の若しくは重水素及び（Ｃ６～Ｃ１８）アリールの少なくとも１つで置換されたカルバゾリル、非置換の若しくは重水素で置換されたジベンゾフラニル、又は非置換の若しくは重水素で置換されたジベンゾチオフェニルを含むことを条件とする］
で表される。

In formula 1-B,
X _a represents O or S;
R ₄₁ to R ₄₈ are each independently hydrogen, deuterium, or unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl (C6-C18 ) aryl, or —L _b —HAr _b , with the proviso that at least one of R ₄₁ to R ₄₈ represents —L _b —HAr _b ;
L _b represents unsubstituted or deuterium-substituted naphthalene;
HAr _b has the following formula 1-b:

[In formula 1-b,
Ar _a and Ar _b are each independently unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterated terphenyl, unsubstituted or deuterated carbazolyl, unsubstituted or deuterated dibenzofuranyl, unsubstituted or deuterated dibenzothiophenyl , or combinations thereof, wherein at least one of Ar _a and Ar _b is carbazolyl unsubstituted or substituted with at least one of deuterium and (C6-C18)aryl, unsubstituted or deuterium or dibenzofuranyl substituted with, or dibenzothiophenyl unsubstituted or substituted with deuterium]
is represented by

ADVANTAGES OF THE INVENTION The organic electroluminescent compounds according to the present disclosure exhibit suitable performance for their use in organic electroluminescent devices. In addition, by including certain compounds according to the present disclosure, or by including certain combinations of compounds according to the present disclosure as multiple host materials, low driving voltages, high luminescence compared to conventional organic electroluminescent devices An organic electroluminescent device is provided that has efficiency and/or excellent lifetime properties, and it is possible to manufacture display systems or lighting systems using it.

4 illustrates a graph showing the increase in bond dissociation energy associated with deuteration.

The present disclosure is described in detail herein below. However, the following description is intended to illustrate the disclosure and is in no way meant to limit the scope of the disclosure.

The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and can optionally be included in any of the layers making up the organic electroluminescent device.

The term "organic electroluminescent material" in this disclosure means a material that can contain at least one chemical compound that can be used in an organic electroluminescent device. Organic electroluminescent materials may optionally be included in any of the layers making up the organic electroluminescent device. For example, organic electroluminescent materials include hole-injecting materials, hole-transporting materials, hole-assisting materials, light-emitting assisting materials, electron-blocking materials, light-emitting materials (including host materials and dopant materials), electron-buffering materials, hole It can be a blocking material, an electron-transporting material, an electron-injecting material, or the like.

The term "host materials" in this disclosure means host materials comprising a combination of at least two compounds that can be included in any light-emitting layer making up an organic electroluminescent device. It can refer both to the material before it is included in the organic electroluminescent device (eg before vapor deposition) and after it is included in the organic electroluminescent device (eg after vapor deposition). For example, a plurality of host materials of the present disclosure is a combination of at least two host materials and can optionally further include conventional materials included in organic electroluminescent materials. At least two compounds included in the plurality of host materials of the present disclosure can be included together in one emissive layer or can be included in different emissive layers. For example, at least two host materials can be mixed or co-evaporated, or can be evaporated separately.

As used herein, the term "(C1-C30)alkyl" means a linear or branched alkyl having 1 to 30 carbon atoms making up the chain, wherein the number of carbon atoms is It is preferably 1-10, more preferably 1-6. The above alkyls can include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl and the like. The term "(C3-C30)cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. The above cycloalkyls can include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl and the like. The term "(3- to 7-membered)heterocycloalkyl" has 3 to 7 ring skeletal atoms and the group consisting of B, N, O, S, Si, P and Se, preferably O, S, It means cycloalkyl containing at least one heteroatom selected from the group consisting of N, and Se. The above cycloalkyls can include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. The term "(C6-C30)aryl" or "(C6-C30)arylene" means a monocyclic or multicyclic radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms. do. The aryl or arylene mentioned above may be partially saturated and may contain a spiro structure. The above aryls include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanth. renyl, benzophenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorenyl]yl, spiro[cyclopentene-fluorene] yl, spiro[dihydroindene-fluorene]yl, azulenyl, tetramethyldihydrophenanthrenyl, and the like. Specifically, the above aryls include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4 -phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl , 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl , dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl , 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m- cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4′-methylbiphenyl, 4″-tert-butyl-p-terphenyl-4-yl, 9,9- dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9- Diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[ a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11- Dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl , 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1 -benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11 , 11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo [b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11 -dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c ] fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl -9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl , 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6 -benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11 , 11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo [b] fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b ] fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl -9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl , 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6 -benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11 , 11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro -2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl and the like. obtain.

The term "(3-30 membered)heteroaryl" or "(3-30 membered)heteroarylene" has 3 to 30 ring skeletal atoms and includes B, N, O, S, Si, P, and It is intended to be aryl or arylene containing at least one, preferably 1 to 4 heteroatoms selected from the group consisting of Se. The heteroaryl or heteroarylene mentioned above may be a monocyclic ring or a fused ring fused with at least one benzene ring; may be partially saturated; It may be formed by joining aryl or aryl groups; it may contain a spiro structure. The above heteroaryls include single aryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl. Cyclic ring heteroaryl; and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofloquinolinyl, benzofloquina Zolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthoflopyrimidinyl, benzothienoquinolyl, benzothienoquinazolinyl, naphthyridinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzo pyrimidoindolyl, benzofuropyrazinyl, naphthoflopyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, Benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazole phenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl fused ring heteroaryls such as aryl, indenocarbazolyl, and the like. More specifically, the above heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2 ,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2 - indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8- imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl , 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1 -isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4 -quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl , 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, Azacarbazol-4-yl, Azacarbazol-5-yl, Azacarbazol-6-yl, Azacarbazol-7-yl, Azacarbazol-8-yl, Azacarbazol-9-yl, 1-phenanthridinyl, 2 -phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 1 0-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl , 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol- 1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4- tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuran nyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b ]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho- [1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]- Benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2 ,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3 -b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-bene Zofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2 ,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho- [1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1 ,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2 -b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b ]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]- Benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothio phenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10- naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7- Benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzo furo[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl 3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3, 2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3- Germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl and the like can be included. Additionally, "halogen" includes F, Cl, Br, and I.

Additionally, “ortho (o-)”, “meta (m-)”, and “para (p-)” are prefixes that each indicate the relative position of a substituent. Ortho indicates that two substituents are adjacent to each other, for example when two substituents in a benzene derivative occupy the 1 and 2 positions, it is called the ortho position. Meta indicates that there are two substituents at the 1 and 3 positions, for example when two substituents in a benzene derivative occupy the 1 and 3 positions, it is called the meta position. Para indicates that the two substituents are at the 1- and 4-positions, for example when the two substituents in a benzene derivative occupy the 1- and 4-positions, it is called the para-position.

As used herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a particular functional group has been replaced with another atom or another functional group, i.e., a substituent, and also includes replacing a hydrogen atom with a group formed by combining two or more of the above substituents. For example, a "group formed by the combination of two or more substituents" can be pyridine-triazine. Thus, a pyridine-triazine may be interpreted as a heteroaryl substituent or as a substituent with two heteroaryl substituents attached. As used herein, substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted dibenzofuranyl, substituted dibenzothiophenyl, substituted carbazolyl, substituted triazinyl, substituted pyridyl, substituted pyrimidinyl, substituted quinazolinyl, substituted benzoquina Zolinyl, substituted quinoxalinyl, substituted benzoquinoxalinyl, substituted quinolyl, substituted benzoquinolyl, substituted isoquinolyl, substituted benzoisoquinolyl, substituted triazolyl, substituted pyrazolyl, substituted napthyridinyl, substituted benzothienopyrimidinyl, substituted pyridopyrazinyl, substituted phenyl, substituted biphenyl , substituted terphenyl, substituted naphthyl, substituted fluorenyl, substituted benzofluorenyl, substituted triphenylenyl, substituted fluoranthenyl, substituted phenanthrenyl, substituted dibenzofuranyl, substituted carbazolyl, and substituted dibenzothiophenyl are each independently , deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy (C6-C30)arylthio; at least one of unsubstituted or deuterium, (C1-C30)alkyl, (C6-C30)aryl, (3-50 membered)heteroaryl, and di(C6-C30)arylamino (3-30 membered) heteroaryl substituted with; unsubstituted or deuterium, cyano, (C1-C30) alkyl, (3-30 membered) heteroaryl, mono- or di-(C6-C30) aryl (C6-C30)aryl substituted with at least one of amino and tri(C6-C30)arylsilyl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30) Alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino mono- or di-(C6-C30) arylamino; mono- or di-(3-30 membered) hete (C1-C30) alkyl(C2-C30) alkenylamino; (C1-C30) alkyl(C6-C30) arylamino; (C1-C30) alkyl(3-30 membered) heteroarylamino; (C2 -C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30) aryl (3-30 membered) heteroarylamino; (C1-C30) alkyl (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylbornyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)aryl (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, the substituents are each independently deuterium; (C1-C20) alkyl unsubstituted or substituted with at least one deuterium; unsubstituted or deuterium; (C6-C25)aryl, and (C6-C25)aryl substituted with at least one of (5-25 membered)heteroaryl; and unsubstituted or with at least one of deuterium and (C6-C25)aryl at least one selected from the group consisting of substituted (5- to 25-membered) heteroaryl; According to another embodiment of the present disclosure, the substituents are each independently deuterium; (C1-C20)alkyl unsubstituted or substituted with at least one deuterium; unsubstituted or deuterium , (C6-C18)aryl, and (C6-C18)aryl substituted with at least one of (5-20 membered)heteroaryl; and at least one of unsubstituted or deuterium and (C6-C18)aryl is at least one selected from the group consisting of (5- to 20-membered) heteroaryl substituted with For example, substituents may be deuterium; methyl; phenyl unsubstituted or substituted with at least one of deuterium, dibenzofuranyl, and carbazolyl; naphthyl unsubstituted or substituted with at least one deuterium; phenylnaphthyl; unsubstituted or substituted with at least one deuterium biphenyl; unsubstituted or substituted with at least one deuterium terphenyl; unsubstituted or with at least one deuterium unsubstituted or substituted with at least one deuterium and phenyl; spirobifluorenyl unsubstituted or substituted with at least one deuterium; unsubstituted or deuterium and dibenzofuranyl substituted with at least one of phenyl; dibenzothiophenyl unsubstituted or substituted with at least one of deuterium and phenyl; carbazolyl unsubstituted or substituted with at least one of deuterium and phenyl and one selected from the group consisting of benzocarbazolyl.

In this disclosure, heteroaryl, heteroarylene, and heterocycloalkyl each independently contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, and Se. obtain. Additionally, the heteroatom may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl , substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6 -C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) ) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3- 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted (C1- C30) alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) heteroarylamino , and substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino.

The plurality of host materials of the present disclosure comprises a first host material and a second host material, the first host material comprising at least one compound represented by Formula 1, wherein the second host material comprises: At least one compound represented by Formula 2 is included.

In Formula 1, X represents O, S or Se.

In Formula 1, HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing a nitrogen atom. HAr preferably contains at least 2 nitrogen atoms, more preferably at least 3 nitrogen atoms. According to one embodiment, HAr is a (5-25 membered) hetero containing a nitrogen atom and unsubstituted or substituted with at least one of (C6-C30) aryl and (3-30 membered) heteroaryl represents aryl. According to another embodiment, HAr is a (5-20 membered)heteroaryl containing a nitrogen atom and unsubstituted or substituted with two (C6-C30)aryls, or (C6-C30)aryl and It represents (3- to 30-membered)heteroaryl. Specifically, HAr is substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted Substituted benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted It may be naphthyridinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted pyridopyrazinyl. substituted triazinyl, substituted pyridyl, substituted pyrimidinyl, substituted quinazolinyl, substituted benzoquinazolinyl, substituted quinoxalinyl, substituted benzoquinoxalinyl, substituted quinolyl, substituted benzoquinolyl, substituted isoquinolyl, substituted benzoisoquinolyl, substituted triazolyl, substituted pyrazolyl, substituted The substituents of naphthyridinyl, substituted benzothienopyrimidinyl, substituted carbazolyl, and substituted pyridopyrazinyl are each independently at least one of unsubstituted or deuterium, tri(C6-C30)arylsilyl, and (3-30 membered)heteroaryl. (C6-C30)aryl substituted with one; or (3-30 membered)aryl unsubstituted or substituted with (C6-C30)aryl. For example, HAr can be substituted triazinyl or substituted pyrimidinyl, wherein the substituted triazinyl and substituted pyrimidinyl substituents are each independently unsubstituted or at least one deuterium, dibenzofuranyl, carbazolyl, phenyl substituted with and triphenylsilyl; naphthyl; naphthylphenyl; phenylnaphthyl; biphenyl unsubstituted or substituted with at least one deuterium; unsubstituted or substituted with at least one deuterium and phenyl dibenzofuranyl; unsubstituted or substituted with at least one deuterium dibenzothiophenyl; unsubstituted or with at least one deuterium and phenyl carbazolyl substituted with ; and benzocarbazolyl optionally further substituted with deuterium.

In Formula 1, L represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment, L represents a single bond or substituted or unsubstituted (C6-C25) arylene. According to another embodiment, L represents a single bond or unsubstituted or deuterium-substituted (C6-C18) arylene. For example, L can be a single bond, unsubstituted or deuterated phenylene, or unsubstituted or deuterated naphthalene.

In Formula 1, R ₁ and R ₂ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or —SiR ₁₁ R ₁₂ R represents ₁₃ . According to one embodiment, R ₁ and R ₂ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl show. According to another embodiment, R ₁ and R ₂ are each independently hydrogen, deuterium, (C6-C25)aryl unsubstituted or substituted with (C6-C18)aryl, or unsubstituted or (5- to 25-membered)heteroaryl substituted with (C6-C18)aryl. For example, R ₁ and R ₂ are each independently hydrogen, deuterium, phenyl, biphenyl, phenyl-substituted fluorenyl, triphenylenyl, spirobifluorenyl, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophenyl, It may be phenyl-substituted carbazolyl, benzothienocarbazolyl, or the like.

R ₁₁ to R ₁₃ each independently represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.

In Formula 1, a represents an integer of 1 to 4, and b represents an integer of 1 to 3, wherein when each of a and b is an integer of 2 or more, each of R ₁ and each of R ₂ may be the same or different.

Formula 1 can be represented by Formula 1-1 below.

In Formula I-1, X, R ₁ , R ₂ , L, a, and b are as defined in Formula 1.

In Formula 1-1, X' ₁ to X' ₃ each independently represent CR' or N, where R' represents hydrogen or deuterium, and at least X' ₁ to X' ₃ Two represent N. In particular, any two of X' ₁ to X' ₃ may be N and the others may be CR'; or all of X' ₁ to X' ₃ may be N.

In Formula 1-1, R ₃ and R ₄ each independently represent substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3- to 30-membered) heteroaryl. R ₃ and R ₄ are the same or different from each other. According to one embodiment, R ₃ and R ₄ each independently represent substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-25 membered) heteroaryl. According to another embodiment, R ₃ and R ₄ are each independently unsubstituted or substituted with at least one of deuterium, tri(C6-C30)arylsilyl and (5-25 membered)heteroaryl (C6-C25)aryl; or (5-25 membered)heteroaryl, unsubstituted or substituted with (C6-C18)aryl. For example, R ₃ and R ₄ are each independently phenyl unsubstituted or substituted with at least one of deuterium, dibenzofuranyl, carbazolyl, and triphenylsilyl; terphenyl; triphenylenyl; diphenylfluorenyl; spirobifluorenyl; unsubstituted or phenyl-substituted dibenzofuranyl; substituted dibenzothiophenyl; unsubstituted or phenyl-substituted carbazolyl; or optionally further substituted with deuterium, benzocarbazolyl, and the like.

Formula 1-1 can be represented by any one of Formulas 1-1-1 to 1-1-4 below.

In Formulas 1-1-1 to 1-1-4, X, X' ₁ to X' ₃ , R ₁ to R ₄ , L, a, and b are as defined in Formula 1.

In Formula 2, A ₁ and A ₂ each independently represent substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl. show. According to one embodiment, A ₁ and A ₂ are each independently substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted represents a substituted carbazolyl. Specifically, A ₁ and A ₂ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl could be. substituted aryl, substituted phenyl, substituted biphenyl, substituted terphenyl, substituted naphthyl, substituted fluorenyl, substituted benzofluorenyl, substituted triphenylenyl, substituted fluoranthenyl, substituted phenanthrenyl, substituted dibenzofuranyl, substituted carbazolyl, and substituted dibenzothiophenyl; Each substituent is independently at least one of deuterium, (C6-C30)aryl, and (3-30 membered)heteroaryl, preferably deuterium, (C6-C18)aryl, and (5-20 ) can be at least one heteroaryl; For example, A ₁ and A ₂ are each independently phenyl unsubstituted or substituted with at least one of deuterium, naphthyl, triphenylenyl, dibenzofuranyl, and dibenzothiophenyl; naphthyl substituted with at least one of phenyl; biphenyl unsubstituted or substituted with at least one deuterium; terphenyl unsubstituted or substituted with at least one deuterium; triphenylenyl substituted with deuterium; dibenzofuranyl unsubstituted or substituted with at least one of deuterium and phenyl; dibenzothiophenyl unsubstituted or substituted with at least one of deuterium and phenyl; or carbazolyl, unsubstituted or substituted with at least one of deuterium, phenyl, and naphthyl.

In Formula 2, X ₁₁ to X ₂₆ each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl. Any one of X ₁₅ to X ₁₈ and any one of X ₁₉ to X ₂₂ are bonded to each other to form a single bond. At least one, preferably two, more preferably three, and even more preferably four of X ₁₁ , X ₁₈ , X ₁₉ and X ₂₆ are deuterium.

According to one embodiment, in the compound of formula 2, the deuterium substitution rate is 90% or more, preferably 94% or more, more preferably 97% or more of the total number of hydrogens. When compounds of Formula 2 are substituted at the aforementioned deuterium substitution ratios, the bond dissociation energy associated with deuteration can be increased to increase compound stability. Organic electroluminescent devices containing said compounds can exhibit improved lifetime properties.

Formula 2 can be represented by any one of Formulas 2-1 to 2-8 below.

In Formulas 2-1 to 2-8, A ₁ , A ₂ and X ₁₁ to X ₂₆ are as defined in Formula 2.

The compound represented by Formula 1 can be at least one selected from the group consisting of the following compounds, but is not limited thereto.

The compound represented by Formula 2 can be at least one selected from the group consisting of the following compounds, but is not limited thereto.

In the above compounds, D _n represents that n number of hydrogens have been replaced with deuterium; n is an integer from 1-50. According to one embodiment, n is an integer greater than or equal to 4, preferably an integer greater than or equal to 6, more preferably an integer greater than or equal to 8, even more preferably an integer greater than or equal to 10. When deuterated to numbers above the lower limit, the bond dissociation energy associated with deuteration can be increased to increase compound stability. When the compounds are used in organic electroluminescent devices, the devices can exhibit improved lifetime properties.

A combination of at least one of compounds H1-1 through H1-381 and at least one of compounds H2-1 through H2-146 can be used in organic electroluminescent devices.

Additionally, the present disclosure provides organic electroluminescent compounds represented by Formula 1-A or 1-B, organic electroluminescent materials comprising the compounds, and organic electroluminescent devices comprising the compounds or materials. The material may consist solely of the organic electroluminescent compounds of the present disclosure, or may further comprise conventional materials contained in organic electroluminescent materials. According to one embodiment, the organic electroluminescent compound represented by formula 1-A or 1-B can be included as a host material in the light-emitting layer, the hole-injection layer, the hole-transport layer, the hole-assist layer, , and at least one of the emission assist layer.

式１－Ａにおいて、
Ｘ_ａは、Ｏ又はＳを表し；
Ｒ_４１～Ｒ_４８は、それぞれ独立して、水素、重水素、又は非置換の若しくは重水素、（Ｃ１～Ｃ６）アルキル及び（Ｃ６～Ｃ１８）アリールの少なくとも１つで置換された（Ｃ６～Ｃ１８）アリールを表すか、又は以下の式１－ａで表され、但し、Ｒ_４１～Ｒ_４８の少なくとも１つは、以下の式１－ａ：

［式１－ａ中、
Ｒａ～Ｒｄは、それぞれ独立して、水素、重水素、又は非置換の若しくは重水素、（Ｃ１～Ｃ６）アルキル及び（Ｃ６～Ｃ１８）アリールの少なくとも１つで置換された（Ｃ６～Ｃ１８）アリールを表し；
Ａｒ_ａ及びＡｒ_ｂは、それぞれ独立して、非置換の若しくは重水素で置換されたフェニル、置換若しくは非置換ナフチル、非置換の若しくは重水素で置換されたビフェニル、非置換の若しくは重水素で置換されたテルフェニル、非置換の若しくは重水素で置換されたカルバゾリル、非置換の若しくは重水素で置換されたジベンゾフラニル、非置換の若しくは重水素で置換されたジベンゾチオフェニル、又はそれらの組合せを表し、但し、Ａｒ_ａ及びＡｒ_ｂの少なくとも１つは、置換若しくは非置換カルバゾリルを表すことを条件とする］
で表されることを条件とする。

In formula 1-A,
X _a represents O or S;
R ₄₁ to R ₄₈ are each independently hydrogen, deuterium, or unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl (C6-C18 ) aryl or represented by formula 1-a below, provided that at least one of R ₄₁ to R ₄₈ is represented by formula 1-a below:

[In formula 1-a,
Ra-Rd are each independently hydrogen, deuterium, or (C6-C18)aryl unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl represents;
Ar _a and Ar _b are each independently unsubstituted or deuterium-substituted phenyl, substituted or unsubstituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted carbazolyl, unsubstituted or deuterium-substituted dibenzofuranyl, unsubstituted or deuterium-substituted dibenzothiophenyl, or combinations thereof with the proviso that at least one of Ar _a and Ar _b represents substituted or unsubstituted carbazolyl]
is expressed as a condition.

For example, in Formula 1-a, Ar _a and Ar _b are each independently phenyl unsubstituted or substituted with at least one of deuterium, dibenzofuranyl and carbazolyl; deuterium-substituted biphenyl; unsubstituted or at least one deuterium-substituted terphenyl; unsubstituted or at least one deuterium-substituted dibenzofuranyl; unsubstituted or at least one or carbazolyl unsubstituted or substituted with at least one of deuterium and phenyl, and the like.

According to one embodiment, in Formula 1-a, at least one of Ar _a and Ar _b can be represented by Formula 1-b1 or 1-b2 below.

In formulas 1-b1 and 1-b2,
La is a single bond, unsubstituted or deuterated phenylene, unsubstituted or deuterated naphthylene, unsubstituted or deuterated biphenylene, or unsubstituted or deuterated representing a substituted terphenylene;
R ₅₁ to R ₅₉ are each independently hydrogen, deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or combinations thereof.

Compounds represented by Formula 1-A include compounds H1-271 to H1-279, H1-281 to H1-289, H1-291 to H1-299, H1-320 to H1-322, and H1-329 to H1 -331 may be at least one selected from the group consisting of, but is not limited to.

式１－Ｂにおいて、
Ｘ_ａは、Ｏ又はＳを表し；
Ｒ_４１～Ｒ_４８は、それぞれ独立して、水素；重水素；非置換の若しくは重水素、（Ｃ１～Ｃ６）アルキル及び（Ｃ６～Ｃ１８）アリールの少なくとも１つで置換された（Ｃ６～Ｃ１８）アリール；又は－Ｌ_ｂ－ＨＡｒ_ｂを表し；但し、Ｒ_４１～Ｒ_４８の少なくとも１は－Ｌ_ｂ－ＨＡｒ_ｂを表すことを条件とし；
Ｌ_ｂは、非置換の若しくは重水素で置換されたナフタレンを表し；
ＨＡｒ_ｂは、以下の式１－ｂ：

［式１－ｂ中、
Ａｒ_ａ及びＡｒ_ｂは、それぞれ独立して、非置換の若しくは重水素で置換されたフェニル、非置換の若しくは重水素で置換されたナフチル、非置換の若しくは重水素で置換されたビフェニル、非置換の若しくは重水素で置換されたテルフェニル、非置換の若しくは重水素で置換されたカルバゾリル、非置換の若しくは重水素で置換されたジベンゾフラニル、非置換の若しくは重水素で置換されたジベンゾチオフェニル、又はそれらの組合せを表し、但し、Ａｒ_ａ及びＡｒ_ｂの少なくとも１つは、非置換の若しくは重水素及び（Ｃ６－Ｃ１８）アリールの少なくとも１つで置換されたカルバゾリル、非置換の若しくは重水素で置換されたジベンゾフラニル、又は非置換の若しくは重水素で置換されたジベンゾチオフェニルを含むことを条件とする］
で表される。

In formula 1-B,
X _a represents O or S;
R ₄₁ to R ₄₈ are each independently hydrogen; deuterium; unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl (C6-C18) or represents -L _b -HAr _b ; with the proviso that at least one of R ₄₁ to R ₄₈ represents -L _b -HAr _b ;
L _b represents unsubstituted or deuterium-substituted naphthalene;
HAr _b has the following formula 1-b:

[In formula 1-b,
Ar _a and Ar _b are each independently unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterated terphenyl, unsubstituted or deuterated carbazolyl, unsubstituted or deuterated dibenzofuranyl, unsubstituted or deuterated dibenzothiophenyl or combinations thereof, provided that at least one of Ar _a and Ar _b is carbazolyl unsubstituted or substituted with at least one of deuterium and (C6-C18)aryl, unsubstituted or deuterium or dibenzofuranyl substituted with, or dibenzothiophenyl unsubstituted or substituted with deuterium]
is represented by

According to one embodiment, R ₄₁ -R ₄₈ each independently represent hydrogen, deuterium or -L _b -HAr _b . According to another embodiment, any one of R ₄₁ -R ₄₈ represents -L _b -HAr _b .

According to one embodiment, in Formula 1-b, Ar _a and Ar _b are each independently phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, biphenyl, terphenyl, unsubstituted or phenyl-substituted dibenzo It may be furanyl, unsubstituted or phenyl-substituted dibenzothiophenyl, or unsubstituted or phenyl-substituted carbazolyl, where phenyl is optionally further substituted with at least one deuterium. According to another embodiment, at least one of Ar _a and Ar _b is carbazolyl unsubstituted or substituted with at least one of deuterium and phenyl, dibenzofuranyl unsubstituted or substituted with deuterium. , or unsubstituted or deuterium-substituted dibenzothiophenyl.

The compound represented by Formula 1-B can be at least one selected from the group consisting of compounds H1-342 to H1-381, but is not limited thereto.

Compounds represented by Formulas 1, 1-A, and 1-B according to the present disclosure can be prepared by synthetic methods known to those skilled in the art, for example, by reference to Reaction Scheme 1 below, but are not limited thereto. not.
[Reaction Scheme 1]

In Reaction Scheme 1, X, HAr, L, R ₁ , R ₂ , a, and b are as defined in Formula 1.

Compounds of Formula 2 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art, for example, by reference to Reaction Scheme 2 below, but are not limited thereto.
[Reaction scheme 2]

In Reaction Scheme 2, A ₁ , A ₂ , X ₁₁ -X ₂₆ , and n are as defined in Formula 2, and Dn represents that n number of hydrogens have been replaced with deuterium.

Exemplary syntheses of compounds represented by Formulas 1, 1-A, 1-B, and 2 of the present disclosure are described above, all of which are known to those skilled in the art by Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont mediated etherification reaction, Miyaura boronation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN _1- substitution reaction, SN _2- substitution reaction, and phosphine-mediated reductive cyclization reaction, etc., and defined in Formulas 1, 1-A, 1-B and 2 above. However, it can be easily understood that the above reaction proceeds even when substituents are attached, which are not specified in specific synthesis examples.

Additionally, deuterated compounds of Formulas 1, 1-A, 1-B, and 2 can be prepared in a similar manner by using deuterated precursor materials, or more generally The non-deuterated compound is treated with a deuterated solvent or D6-benzene in the presence of an H/D exchange catalyst such as a Lewis acid such as aluminum trichloride or ethylaluminum chloride, trifluoromethanesulfonic acid, or trifluoromethanesulfonic acid-D. can be prepared by treatment with Additionally, the degree of deuteration can be controlled by varying reaction conditions such as reaction temperature. For example, the number of deuterium atoms in Formulas 1, 1-A, 1-B, and 2 can be controlled by adjusting reaction temperature and time, acid equivalents, and the like.

The present disclosure is an organic electroluminescent device comprising an anode, a cathode, and at least one emissive layer between the anode and cathode, wherein the at least one emissive layer comprises a plurality of host materials according to the present disclosure. I will provide a. A first host material and a second host material according to the present disclosure may be contained in one light-emitting layer, or may each be contained in different light-emitting layers. The ratio of the compound of Formula 1 to the compound of Formula 2 in the plurality of host materials is from about 1:99 to about 99:1, preferably from about 10:90 to about 90:10, more Preferably from about 30:70 to about 70:30. In addition, the compound of formula 1 and the compound of formula 2 in the desired ratio can be prepared by mixing them in a shaker, by melting them with heat in a glass tube, or by dissolving them in a solvent or the like.

According to one embodiment, the doping concentration of the dopant compound to the host compound in the light-emitting layer can be less than 20% by weight. The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant materials applied to the organic electroluminescent device of the present disclosure are not particularly limited, but are preferably metalized complexes of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) compounds, more preferably selected from the group consisting of ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), even more preferably It can be an ortho-metallated iridium complex compound.

Dopants included in the organic electroluminescent devices of the present disclosure can be, but are not limited to, compounds represented by Formula 101 below.

Ｒ_１００～Ｒ_１０３は、それぞれ独立して、水素、重水素、ハロゲン、非置換の又は重水素及び／若しくはハロゲンで置換された（Ｃ１～Ｃ３０）アルキル、置換若しくは非置換（Ｃ３～Ｃ３０）シクロアルキル、置換若しくは非置換（Ｃ６～Ｃ３０）アリール、シアノ、置換若しくは非置換（３～３０員）ヘテロアリール、又は置換若しくは非置換（Ｃ１～Ｃ３０）アルコキシを表すか；或いは隣接する置換基と結合して、ピリジンと一緒に、環、例えば、置換若しくは非置換の、キノリン、ベンゾフロピリジン、ベンゾチエノピリジン、インデノピリジン、ベンゾフロキノリン、ベンゾチエノキノリン、又はインデノキノリンを形成し得；
Ｒ_１０４～Ｒ_１０７は、それぞれ独立して、水素、重水素、ハロゲン、非置換若しくは重水素及び／若しくはハロゲンで置換された（Ｃ１～Ｃ３０）アルキル、置換若しくは非置換（Ｃ３～Ｃ３０）シクロアルキル、置換若しくは非置換（Ｃ６～Ｃ３０）アリール、置換若しくは非置換（３～３０員）ヘテロアリール、シアノ、又は置換若しくは非置換（Ｃ１～Ｃ３０）アルコキシを表すか；或いは隣接する置換基と結合して、ベンゼンと一緒に、置換若しくは非置換環、例えば、置換若しくは非置換の、ナフタレン、フルオレン、ジベンゾチオフェン、ジベンゾフラン、インデノピリジン、ベンゾフロピリジン、又はベンゾチエノピリジンを形成し得、
Ｒ_２０１～Ｒ_２２０は、それぞれ独立して、水素、重水素、ハロゲン、非置換の又は重水素及び／若しくはハロゲンで置換された（Ｃ１～Ｃ３０）アルキル、置換若しくは非置換（Ｃ３～Ｃ３０）シクロアルキル、又は置換若しくは非置換（Ｃ６～Ｃ３０）アリールを表すか；或いは隣接する置換基と結合して置換若しくは非置換環を形成し得；
ｓは、１～３の整数を表す。 In Equation 101,
L' is selected from Structures 1-3 below:

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, unsubstituted or deuterium and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cyclo represents alkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or bonded to adjacent substituents together with pyridine may form a ring, such as a substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline;
R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, unsubstituted or deuterium and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl , substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; with benzene can form a substituted or unsubstituted ring, such as substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothienopyridine,
R ₂₀₁ to R ₂₂₀ are each independently hydrogen, deuterium, halogen, unsubstituted or deuterium and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cyclo represents alkyl, or substituted or unsubstituted (C6-C30) aryl; or may be joined with adjacent substituents to form a substituted or unsubstituted ring;
s represents an integer of 1 to 3;

Specific non-limiting examples of dopant compounds are as follows.

An organic electroluminescent device according to the present disclosure has an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer includes a light-emitting layer, a hole-injecting layer, a hole-transporting layer, a hole-assisting layer, a light-emitting-assisting layer, an electron-transporting layer, an electron-buffering layer, an electron-injecting layer, an intermediate layer, a hole-blocking layer, and an electron It may further comprise at least one layer selected from the group consisting of blocking layers. Each of the layers may be further configured as multiple layers.

The anode and cathode may each be formed of a transparent conductive material, or a semitransparent or reflective conductive material. Organic electroluminescent devices can be top-emitting, bottom-emitting, or dual-emitting, depending on the materials forming the anode and cathode. Additionally, the hole injection layer may be further doped with a p-type dopant and the electron injection layer may be further doped with an n-type dopant.

The organic layer may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.

Further, in the organic electroluminescent device of the present disclosure, the organic layer comprises Group 1 metals, Group 2 metals, Period 4 transition metals, Period 5 transition metals, lanthanides, and d- It may further comprise at least one metal selected from the group consisting of organic metals of transition elements, or at least one complex compound containing a metal.

In addition, the organic electroluminescent device of the present disclosure can emit white light by further comprising at least one emissive layer comprising blue, red, or green electroluminescent compounds known in the art in addition to the compounds of the present disclosure. can emit light. Optionally it may further comprise a yellow or orange emitting layer.

In the organic electroluminescent device of the present disclosure, preferably at least one layer selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") is It may be placed on the inner surface of one or both electrodes. Specifically, a silicon or aluminum chalcogenide (including oxide) layer is preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide or metal oxide layer is preferably the electroluminescent medium layer. positioned on the cathode surface of the media layer. Such surface layers provide operational stability to organic electroluminescent devices. Preferably, chalcogenides include _SiOx (1≤X≤2), _AlOx (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, _MgF2 , _CaF2. , rare earth metal fluorides and the like; metal oxides include _Cs2O , _Li2O , MgO, SrO, BaO, CaO and the like.

A hole-injecting layer, a hole-transporting layer, an electron-blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer can be multiple layers to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, where each of the multiple layers contains two compounds. can be used simultaneously. A hole-transporting layer or an electron-blocking layer can also be multilayered.

Electron buffer layers, hole blocking layers, electron transport layers, electron injection layers, or combinations thereof can be used between the light emitting layer and the cathode. The electron buffer layer can be multiple layers to control electron injection and improve interfacial properties between the light emitting layer and the electron injection layer, where each of the multiple layers uses two compounds simultaneously. can. A hole-blocking layer or electron-transporting layer may also be multilayers, where each of the multilayers may employ multiple compounds.

The emission-assisting layer can be placed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When an emission-assisting layer is placed between the anode and the light-emitting layer, it can be used to facilitate hole injection and/or hole transport, or to prevent electron overflow. When an emission-assisting layer is placed between the cathode and the light-emitting layer, it can be used to facilitate electron injection and/or electron transport, or to prevent hole overflow. Also, a hole assist layer can be disposed between the hole transport layer (or hole injection layer) and the emissive layer and is effective to promote or inhibit the hole transport rate (or hole injection rate). , thereby allowing the charge balance to be controlled. In addition, an electron blocking layer can be disposed between the hole transport layer (or hole injection layer) and the emissive layer to confine excitons within the emissive layer by blocking the overflow of electrons from the emissive layer. It is possible to prevent leakage of light emission. When the organic electroluminescent device comprises more than one hole-transporting layer, the further included hole-transporting layers can be used as hole-helping layers or electron-blocking layers. Emission-assisting layers, hole-assisting layers or electron-blocking layers can have the effect of improving the efficiency and/or lifetime of organic electroluminescent devices.

Additionally, in the organic electroluminescent device of the present disclosure, the mixed region of the electron transport compound and the reducing dopant or the mixed region of the hole transport compound and the oxidizing dopant is on the surface of at least one of the pairs of electrodes. can be placed. In this case, the electron transport compound is reduced to an anion, which makes it easier to inject and transport electrons from the mixed region into the luminescent medium. In addition, the hole transport compound is oxidized to cations, making it easier to inject and transport holes from the mixed region into the light-emitting medium. Preferably, oxidizing dopants include various Lewis acids and acceptor compounds; reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Reducible dopant layers can be used as charge generating layers to produce organic electroluminescent devices that have two or more emissive layers and emit white light.

Organic electroluminescent materials according to the present disclosure can be used as light-emitting materials for white organic light-emitting devices. White organic light-emitting devices can be side-by-side or stacked, depending on the arrangement of R (red), G (green) or YG (yellow-green), and B (blue) light-emitting parts, or color conversion material (CCM) methods, etc. have been proposed to have various structures such as Organic electroluminescent materials according to the present disclosure may also be used in organic electroluminescent devices including quantum dots (QDs).

Dry film forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or inkjet printing, nozzle printing, slot coating, spin coating, dip coating to form each layer of the organic electroluminescent devices of the present disclosure. Wet film forming methods such as flow coating methods and the like can be used. When the first and second host compounds of the present disclosure are used to form a film, a co-evaporation method or mixed evaporation method is carried out.

When wet film forming methods are used, the thin films can be formed by dissolving or diffusing the materials forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, and the like. The solvent can be anything that can dissolve or diffuse the materials forming each layer and that has no problem with the ability to form a film.

In addition, by using the organic electroluminescent devices of the present disclosure, display systems, such as display systems for smart phones, tablets, notebooks, PCs, TVs, or automobiles; or lighting systems, such as outdoor or indoor lighting. It is possible to manufacture the system.

Hereinafter, methods for preparing compounds according to the present disclosure and their properties, as well as properties of organic electroluminescent devices (OLEDs) comprising multiple host materials according to the present disclosure, are detailed with respect to representative compounds of the present disclosure. explained. However, the disclosure is not limited by the following examples.

１０．５ｇの２－クロロ－４，６－ジフェニル－１，３，５－トリアジン（３９．３ｍｍｏｌ）、１０ｇのジベンゾ［ｂ，ｄ］フラン－１－イルボロン酸（４７．１ｍｍｏｌ）、２．２７ｇのＰｄ（ＰＰｈ_３）_４（１．９６ｍｍｏｌ）、１０．８ｇのＫ_２ＣＯ_３（７８．６ｍｍｏｌ）、２００ｍＬのトルエン、２０ｍＬのＥｔＯＨ、及び４０ｍＬのＨ_２Ｏをフラスコに添加し、１６０℃で撹拌した。反応の終了後に、ＭｅＯＨを混合物に添加した。混合物を撹拌し、溶媒を減圧下での濾過によって除去した。残留物をカラムクロマトグラフィーによって分離した。次いで、ＭｅＯＨを添加し、結果として生じた固体を減圧下で濾過して１２．０ｇの化合物Ｈ１－１（収率：７６．９％）を得た。 Example 1: Preparation of Compound H1-1

10.5 g 2-chloro-4,6-diphenyl-1,3,5-triazine (39.3 mmol), 10 g dibenzo[b,d]furan-1-ylboronic acid (47.1 mmol), 2.27 g of Pd(PPh ₃ ) ₄ (1.96 mmol), 10.8 g K ₂ CO ₃ (78.6 mmol), 200 mL toluene, 20 mL EtOH, and 40 mL H ₂ O were added to the flask and heated at 160° C. Stirred. After completion of the reaction, MeOH was added to the mixture. The mixture was stirred and the solvent was removed by filtration under reduced pressure. The residue was separated by column chromatography. MeOH was then added and the resulting solid was filtered under reduced pressure to give 12.0 g of compound H1-1 (yield: 76.9%).

フラスコ中で、ジベンゾ［ｂ，ｄ］フラン－１－イルボロン酸（２．８ｇ、１３．４５ｍｍｏｌ）、２－（［１，１’－ビフェニル］－４－イル）－４－クロロ－６－フェニル－１，３，５－トリアジン（４．６ｇ、１３．４５ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム（０）（Ｐｄ（ＰＰｈ_３）_４）（０．７７ｇ、０．６７ｍｍｏｌ）、及び２Ｍ炭酸カリウム（４．６ｇ、３３．６ｍｍｏｌ）を、７０ｍＬのトルエン及び１７ｍＬのエタノールに溶解させ、１２０℃で５時間還流させた。反応の終了後に、有機層を酢酸エチルで抽出し、残留水分を硫酸マグネシウムで除去した。次いで、有機層を乾燥させ、カラムクロマトグラフィーによって分離して化合物Ｈ１－２（４．８ｇ、収率：７５％）を得た。 Example 2: Preparation of compound H1-2

In a flask dibenzo[b,d]furan-1-ylboronic acid (2.8 g, 13.45 mmol), 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl -1,3,5-triazine (4.6 g, 13.45 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh ₃ ) ₄ ) (0.77 g, 0.67 mmol), and 2M potassium carbonate (4.6 g, 33.6 mmol) was dissolved in 70 mL of toluene and 17 mL of ethanol and refluxed at 120° C. for 5 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate and residual water was removed with magnesium sulfate. The organic layer was then dried and separated by column chromatography to give compound H1-2 (4.8 g, yield: 75%).

化合物３－１（５ｇ、１８．１ｍｍｏｌ）、２－［１，１’－ビフェニル］－４－イル－４－クロロ－６－フェニル－１，３，５－トリアジン（６．２ｇ、１８．１ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム（０）（１．０５ｇ、０．９０９ｍｍｏｌ）、炭酸カリウム（６．２ｇ、４５．４ｍｍｏｌ）、９０ｍＬのトルエン、２３ｍＬのエタノール、及び２３ｍＬの蒸留水を反応器に添加し、還流下で５時間撹拌した。反応の終了後に、混合物を蒸留水で洗浄し、有機層を酢酸エチルで抽出した。残留水分を硫酸マグネシウムで除去した。次いで、残留物を乾燥させ、カラムクロマトグラフィーによって分離して化合物Ｈ１－１４２（８ｇ、収率：８３％）を得た。 Example 3: Preparation of compound H1-142

Compound 3-1 (5 g, 18.1 mmol), 2-[1,1′-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-triazine (6.2 g, 18.1 mmol ), tetrakis(triphenylphosphine)palladium(0) (1.05 g, 0.909 mmol), potassium carbonate (6.2 g, 45.4 mmol), 90 mL toluene, 23 mL ethanol, and 23 mL distilled water in a reactor. and stirred under reflux for 5 hours. After completion of the reaction, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. Residual moisture was removed with magnesium sulfate. The residue was then dried and separated by column chromatography to give compound H1-142 (8 g, yield: 83%).

Example 4: Preparation of compound H1-242

Synthesis of Compound D4-1 Compound 4-1 (8.5 g, 36.77 mmol), 85 mL of benzene-D6, and trifluoromethanesulfonic acid (8.5 mL, 96.28 mmol) were added to a reactor and Stirred for 3 hours. The mixture was cooled to room temperature and 8.5 mL of _D2O was added. The mixture was stirred for 10 minutes and neutralized with _{aqueous K3PO4} . The organic layer was extracted with ethyl acetate and residual water was removed with magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound D4-1 (8.2 g, yield: 93%).

Synthesis of Compound D4-2 Compound D4-1 (7.2 g, 30.1 mmol) and 150 mL of tetrahydrofuran were added to a reactor under nitrogen atmosphere and cooled to -78°C. Then n-butyllithium (14 mL, 36.1 mmol) was slowly added dropwise. Trimethyl borate (8.1 mL, 72.2 mmol) was added dropwise. The mixture was allowed to react at room temperature for 12 hours. After completion of the reaction, the reaction was quenched with water, the organic layer was extracted with ethyl acetate, and residual water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to give compound D4-2 (1.7 g, yield: 20%).

Synthesis of Compound H1-242 Compound D4-2 (1.7 g, 6.03 mmol), 2-[1,1′-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-triazine (2.1 g, 6.33 mmol), tetrakis(triphenylphosphine)palladium(0) (0.35 g, 0.30 mmol), potassium carbonate (2.1 g, 15.1 mmol), 30 mL toluene, 8 mL ethanol, and 8 mL of distilled water were added to the reactor and stirred under reflux for 4 hours. After completion of the reaction, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. Residual water in the organic layer was removed with magnesium sulfate. The residue was dried and separated by column chromatography to give compound H1-242 (2.1 g, yield: 65%).

フラスコ中で、化合物Ａ（６．０ｇ、１６．２０ｍｍｏｌ）、化合物Ｂ（６．４ｇ、１７．８３ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．９ｇ、０．８１ｍｍｏｌ）、及びＫ_２ＣＯ_３（４．５ｇ、３２．４ｍｍｏｌ）を、８１ｍＬのトルエン、２０ｍＬのＥｔＯＨ、及び２０ｍＬのＨ_２Ｏに溶解させ、還流下で４時間撹拌した。混合物を室温まで冷却した。生成した固体を含有する反応物にＨ_２Ｏを添加した。混合物を３０分間撹拌し、濾過し、カラムクロマトグラフィーによって分離して化合物Ｈ１－２７１（７．０ｇ、収率：７７％）を得た。 Example 5: Preparation of compound H1-271

In a flask, compound A (6.0 g, 16.20 mmol), compound B (6.4 g, 17.83 mmol), Pd _{( PPh3} ) ₄ (0.9 g, 0.81 mmol), and _K2CO3 ( 4.5 g, 32.4 mmol) was dissolved in 81 mL toluene, 20 mL EtOH, and 20 mL H ₂ O and stirred under reflux for 4 hours. The mixture was cooled to room temperature. _H2O was added to the reaction containing the solid that formed. The mixture was stirred for 30 minutes, filtered and separated by column chromatography to give compound H1-271 (7.0 g, yield: 77%).

フラスコ中で、ジベンゾ［ｂ，ｄ］フラン－１－イルボロン酸（５ｇ、１８．３６ｍｍｏｌ）、化合物Ｃ（１０．０ｇ、２３．８１ｍｍｏｌ）、Ｐｄ（ＯＡｃ）_２（５３５ｍｇ、２．３８ｍｍｏｌ）、Ｓｐｈｏｓ（１．９ｇ、４．７６ｍｍｏｌ）、及びＣｓ_２ＣＯ_３（２３ｇ、７１．４ｍｍｏｌ）を、１２０ｍＬのｏ－キシレン、３０ｍＬの１，４－ジオキサン、及び３０ｍＬのＨ_２Ｏに溶解させ、還流下で３時間撹拌した。混合物を室温まで冷却した。生成した固体を含有する反応物にＨ_２Ｏを添加した。混合物を３０分間撹拌し、濾過し、カラムクロマトグラフィーによって分離して化合物Ｈ１－１９２（７．１ｇ、収率：５４％）を得た。 Example 6: Preparation of Compound H1-192

In a flask dibenzo[b,d]furan-1-ylboronic acid (5 g, 18.36 mmol), compound C (10.0 g, 23.81 mmol), Pd(OAc) ₂ (535 mg, 2.38 mmol), Sphos (1.9 g, 4.76 mmol), and Cs ₂ CO ₃ (23 g, 71.4 mmol) were dissolved in 120 mL o-xylene, 30 mL 1,4-dioxane, and 30 mL H ₂ O and refluxed. and stirred for 3 hours. The mixture was cooled to room temperature. _H2O was added to the reaction containing the solid that formed. The mixture was stirred for 30 minutes, filtered and separated by column chromatography to give compound H1-192 (7.1 g, yield: 54%).

フラスコ中で、ジベンゾ［ｂ，ｄ］フラン－３－イルボロン酸（１１．１ｇ、２５．７２ｍｍｏｌ）、化合物Ｄ（６．０ｇ、２８．３ｍｍｏｌ）、Ｐｄ（ＯＡｃ）_２（０．５７ｇ、２．５７ｍｍｏｌ）、Ｓ－Ｐｈｏｓ（０．５２ｇ、５．４５ｍｍｏｌ）、及びＮａＯｔＢｕ（７．４ｇ、７７．１６ｍｍｏｌ）を、１３０ｍＬのｏ－キシレン、３２ｍＬの１，４－ジオキサン、及び３２ｍＬのＨ_２Ｏに溶解させ、還流下で４時間撹拌した。混合物を室温まで冷却した。生成した固体を含有する反応物にＨ_２Ｏを添加した。混合物を３０分間撹拌し、濾過し、カラムクロマトグラフィーによって分離して化合物Ｈ１－２８１（７．８ｇ、収率：５３％）を得た。 Example 7: Preparation of compound H1-281

In a flask, dibenzo[b,d]furan-3-ylboronic acid (11.1 g, 25.72 mmol), compound D (6.0 g, 28.3 mmol), Pd(OAc) ₂ (0.57 g, 2.5 mmol). 57 mmol), S-Phos (0.52 g, 5.45 mmol), and NaOtBu (7.4 g, 77.16 mmol) in 130 mL o-xylene, 32 mL 1,4-dioxane, and 32 mL _H2O . Dissolved and stirred under reflux for 4 hours. The mixture was cooled to room temperature. _H2O was added to the reaction containing the solid that formed. The mixture was stirred for 30 minutes, filtered and separated by column chromatography to give compound H1-281 (7.8 g, yield: 53%).

フラスコ中で、化合物Ａ（３．８ｇ、９．４５ｍｍｏｌ）、９，９’－（６－クロロ－１，３，５－トリアジン－２，４－ジイル）ビス（９Ｈ－カルバゾール）（３．８ｇ、８．５９ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．５ｇ、０．４２ｍｍｏｌ）、及びＫ_２ＣＯ_３（２．９ｇ、２１．４７ｍｍｏｌ）を、４０ｍＬのトルエン、２０ｍＬのＥｔＯＨ、及び２０ｍＬのＨ_２Ｏに溶解させ、還流下で４時間還流した。混合物を室温まで冷却した。生成した固体を含有する反応物にＨ_２Ｏを添加した。混合物を３０分間撹拌し、濾過し、カラムクロマトグラフィーによって分離して化合物Ｈ１－２７５（４．２ｇ、収率：７５％）を得た。 Example 8: Preparation of compound H1-275

In a flask, compound A (3.8 g, 9.45 mmol), 9,9′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (3.8 g) , 8.59 mmol), Pd( _PPh3 ) ₄ (0.5 g, 0.42 mmol), and _K2CO3 (2.9 g, 21.47 mmol) in 40 mL _toluene , 20 mL EtOH, and 20 mL H ₂ O and refluxed under reflux for 4 hours. The mixture was cooled to room temperature. _H2O was added to the reaction containing the solid that formed. The mixture was stirred for 30 minutes, filtered and separated by column chromatography to give compound H1-275 (4.2 g, yield: 75%).

フラスコ中で、化合物Ａ（３．７ｇ、８．５９ｍｍｏｌ）、３－（４－クロロ－６－フェニル－１，３，５－トリアジン－２－イル）－９－フェニル－９Ｈ－カルバゾール（３．５ｇ、９．４５ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．５ｇ、０．４２ｍｍｏｌ）、及びＫ_２ＣＯ_３（２．９ｇ、１１．０６ｍｍｏｌ）を、４０ｍＬのトルエン、２０ｍＬのエタノール、及び２０ｍＬのＨ_２Ｏに溶解させ、還流下で４時間撹拌した。混合物を室温まで冷却した。生成した固体を含有する反応物にＨ_２Ｏを添加した。混合物を３０分間撹拌し、濾過し、カラムクロマトグラフィーによって分離して化合物Ｈ１－２７７（２．８ｇ、収率：５１％）を得た。 Example 9: Preparation of compound H1-277

In a flask, compound A (3.7 g, 8.59 mmol), 3-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole (3. 5 g, 9.45 mmol), Pd( _PPh3 ) ₄ (0.5 g, 0.42 mmol), and _K2CO3 (2.9 g, 11.06 mmol) in 40 mL _toluene , 20 mL ethanol, and 20 mL Dissolved in H ₂ O and stirred at reflux for 4 hours. The mixture was cooled to room temperature. _H2O was added to the reaction containing the solid that formed. The mixture was stirred for 30 minutes, filtered and separated by column chromatography to give compound H1-277 (2.8 g, yield: 51%).

フラスコ中で、化合物Ｃ（１３．２ｇ、３１．４４ｍｍｏｌ）、ジベンゾ［ｂ，ｄ］フラン－３－イルボロン酸（８．０ｇ、３７．７３ｍｍｏｌ）、Ｐｄ（ＯＡｃ）_２（０．７ｇ、３．１４ｍｍｏｌ）、ｓ－Ｐｈｏｓ（２．６ｇ、６．２８ｍｍｏｌ）、及びＣｓ_２ＣＯ_３（３０．７ｇ、９４．３２ｍｍｏｌ）を、１５７ｍＬのｏ－キシレン、４０ｍＬの１１，４－ジオキサン、及び４０ｍＬのＨ_２Ｏに溶解させ、還流下で４時間撹拌した。混合物を室温まで冷却した。生成した固体を含有する反応物にＨ_２Ｏを添加した。混合物を３０分間撹拌し、濾過し、カラムクロマトグラフィーによって分離して化合物Ｈ１－２６２（６．７ｇ、収率：３９％）を得た。 Example 10: Preparation of Compound H1-262

In a flask, compound C (13.2 g, 31.44 mmol), dibenzo[b,d]furan-3-ylboronic acid (8.0 g, 37.73 mmol), Pd(OAc) ₂ (0.7 g, 3. 14 mmol), s-Phos (2.6 g, 6.28 mmol), and Cs ₂ CO ₃ (30.7 g, 94.32 mmol) were combined with 157 mL o-xylene, 40 mL 11,4-dioxane, and 40 mL H ₂ O and stirred at reflux for 4 hours. The mixture was cooled to room temperature. _H2O was added to the reaction containing the solid that formed. The mixture was stirred for 30 minutes, filtered and separated by column chromatography to give compound H1-262 (6.7 g, yield: 39%).

フラスコ中で、化合物Ｈ－Ａ（１５．０ｇ、４２．９ｍｍｏｌ）を熱によって９００ｍＬのベンゼン－Ｄ６に溶解させた。トリフル酸（２５．４ｍＬ、１６９．５ｍｍｏｌ）を６０℃で添加した。３時間後に、混合物を室温まで冷却し、３０ｍＬのＤ_２Ｏを添加した。混合物を１０分間撹拌し、Ｋ_３ＰＯ_４水溶液で中和した。有機層を酢酸エチルで抽出し、残留水分を硫酸マグネシウムで除去した。残留物を減圧蒸留し、カラムクロマトグラフィーによって分離して化合物Ｈ２－５０－Ｄ２５（１２ｇ、収率：７７．０％）を得た。 Example 11: Preparation of Compound H2-50-D25

In a flask, compound HA (15.0 g, 42.9 mmol) was thermally dissolved in 900 mL of benzene-D6. Triflic acid (25.4 mL, 169.5 mmol) was added at 60°C. After 3 hours, the mixture was cooled to room temperature and 30 mL of _D2O was added. The mixture was stirred for 10 minutes and neutralized with _{aqueous K3PO4} . The organic layer was extracted with ethyl acetate and residual water was removed with magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound H2-50-D25 (12 g, yield: 77.0%).

フラスコ中で、化合物Ｈ－Ｂ（２５．０ｇ、４４．６２ｍｍｏｌ）を熱によって６００ｍＬのベンゼン－Ｄ６に溶解させた。トリフル酸（７５ｍＬ、８３４．６ｍｍｏｌ）を４０℃で添加した。３時間３０分後に、混合物を室温まで冷却し、２５ｍＬのＤ_２Ｏを添加した。混合物を１０分間撹拌し、Ｋ_３ＰＯ_４水溶液で中和した。有機層を酢酸エチルで抽出し、減圧留去し、カラムクロマトグラフィーによって分離し、トルエンで再結晶して化合物Ｈ２－２－Ｄ２２（１７．８ｇ、収率：６８．５６％）を得た。 Example 12: Preparation of Compound H2-2-D22

In a flask, compound HB (25.0 g, 44.62 mmol) was thermally dissolved in 600 mL of benzene-D6. Triflic acid (75 mL, 834.6 mmol) was added at 40°C. After 3 hours 30 minutes, the mixture was cooled to room temperature and 25 mL of _D2O was added. The mixture was stirred for 10 minutes and neutralized with _{aqueous K3PO4} . The organic layer was extracted with ethyl acetate, evaporated under reduced pressure, separated by column chromatography, and recrystallized with toluene to obtain compound H2-2-D22 (17.8 g, yield: 68.56%).

Example 13: Preparation of Compound H1-356

Synthesis of Compound 13-3 Compound 13-1 (20.0 g, 82.81 mmol), Compound 13-2 (25.2 g, 99.37 mmol), PdCl ₂ (PPh ₃ ) ₂ (1.2 g, 1.66 mmol) , and KOAc (16.3 g, 165.62 mmol) were dissolved in 415 mL of 1,4-dioxane and stirred under reflux for 3 hours. The mixture was cooled to room temperature, separated layers (MC/H ₂ O), filtered through celite, filtered through silica to give compound 13-3 (24.3 g, yield: 101.7%) in oil phase. .

Synthesis of Compound 13-5 Compound 13-3 (24.3 g, 84.20 mmol), Compound 13-4 (33.1 g, 92.62 mmol), Pd(PPh ₃ ) ₄ (4.9 g, 4.21 mmol), and K ₂ CO ₃ (23.3 g, 168.4 mmol) were dissolved in 420 mL toluene, 105 mL EtOH, and 105 mL H ₂ O and stirred under reflux for 3 hours. The mixture was cooled to room temperature. _H2O was added to the reaction containing the solid that formed. The mixture was stirred for 30 minutes, filtered and separated by column chromatography to give compound 13-5 (12.1 g, yield: 29.7%).

Synthesis of Compound H1-356 Compound 13-5 (5.0 g, 10.33 mmol), Compound 13-6 (3.9 g, 18.59 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.52 mmol), S-Phos (0.4 g, 1.03 mmol) and K ₃ PO ₄ (5.5 g, 25.82 mmol) were dissolved in 52 mL of o-xylene and stirred under reflux for 2 hours. The mixture was cooled to room temperature. H ₂ O was added to the reaction containing the resulting solids and stirred for 30 minutes. The solid was then filtered. The filtrate was separated by column chromatography and recrystallized to obtain compound H1-356 (4.4 g, yield: 69.1%).

化合物１３－５（５．０ｇ、１０．３３ｍｍｏｌ）、化合物１４－１（４．４ｇ、２０．６６ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．５２ｍｍｏｌ）、Ｓ－Ｐｈｏｓ（０．４ｇ、１．０３ｍｍｏｌ）、及びＫ_３ＰＯ_４（５．５ｇ、２５．８２ｍｍｏｌ）を、５２ｍＬのｏ－キシレンに溶解させ、還流下で２時間撹拌した。混合物を室温まで冷却した。生成した固体を含有する反応物にＨ_２Ｏを添加し、混合物を３０分間撹拌した。次いで、固体を濾過した。濾液をカラムクロマトグラフィーによって分離し、再結晶して化合物Ｈ１－３４３（２．４ｇ、収率：３７．７％）を得た。 Example 14: Preparation of Compound H1-343

Compound 13-5 (5.0 g, 10.33 mmol), Compound 14-1 (4.4 g, 20.66 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.52 mmol), S-Phos (0.52 mmol). 4 g, 1.03 mmol), and K ₃ PO ₄ (5.5 g, 25.82 mmol) were dissolved in 52 mL of o-xylene and stirred under reflux for 2 hours. The mixture was cooled to room temperature. H ₂ O was added to the reaction containing the resulting solids and the mixture was stirred for 30 minutes. The solid was then filtered. The filtrate was separated by column chromatography and recrystallized to obtain compound H1-343 (2.4 g, yield: 37.7%).

Device Examples 1-3: Fabrication of OLEDs Comprising Multiple Host Materials According to the Present Disclosure OLEDs were fabricated according to the present disclosure. Transparent electrode indium tin oxide (ITO) thin films (10Ω/sq) on glass substrates for OLED (Geomatech Co., Ltd., Japan) were sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol and then stored in isopropanol. . Then, the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum evaporator and compound HT-1 was introduced into another cell of the vacuum evaporator. The two materials were evaporated at different rates, and compound HI-1 was evaporated with a doping amount of 3% by weight based on the total amount of compound HI-1 and compound HT-1 to form a thickness of 10 nm on the ITO substrate. A hole injection layer having Compound HT-1 was then deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Compound HT-2 was then introduced into another cell of a vacuum vapor deposition apparatus, and a current was passed through the cell to evaporate, thereby forming a second hole-transporting layer having a thickness of 30 nm on the first hole-transporting layer. formed. After forming the hole-injecting layer and the hole-transporting layer, a light-emitting layer was formed thereon as follows: First and second host materials shown in Table 1 below were used as hosts in two vacuum deposition devices. was introduced into one cell and compound D-130 was introduced as a dopant into another cell. The two host materials are evaporated at different ratios of 2:1, the dopant materials are evaporated simultaneously at different ratios, the dopants are evaporated at a doping amount of 10% by weight based on the total amount of the host and dopants, and the second positive electrode is formed. A light emitting layer having a thickness of 40 nm was formed on the hole transport layer. Compound ET-1 and compound EI-1 were evaporated at a weight ratio of 40:60 to form an electron transport layer having a thickness of 35 nm on the light emitting layer. After depositing compound EI-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer by another vacuum deposition apparatus. Thus, an OLED was produced. All materials used to fabricate OLEDs were purified by vacuum sublimation at 10 ⁻⁶ Torr.

Comparative Example 1 Preparation of OLED Containing Comparative Compounds as Host OLEDs were fabricated in the same manner as

Driving voltage, luminous efficiency, and emission color at a luminance of 1,000 nits, and luminance from 100% to 95% at a luminance of 20,000 nits for the OLEDs produced in Device Examples 1-3 and Comparative Example 1. Table 1 below shows the time (lifetime, T95) required to decrease to .

Device Examples 4-17: Fabrication of OLEDs Comprising Multiple Host Materials According to the Present Disclosure Substituting Compound HT-3 for Compound HT-2 as the Second Hole-Transporting Layer, and Using Compound HT-3 as the Host for the Emissive Layer An OLED was fabricated in the same manner as in Device Example 1, except that the first and second host compounds shown in Tables 2 and 3 were used.

Comparative Examples 2-15 Fabrication of OLEDs Containing Comparative Compounds as Hosts Device Examples 4-15, respectively, except compound HB was used instead of compound H2-2-D22 as the second host in the emissive layer. OLEDs were fabricated in the same manner as in 17.

The emission color of the OLEDs produced in Device Examples 4-15 and Comparative Examples 2-13 and the time required for the luminance to drop from 100% to 80% at a luminance of 60,000 nits (lifetime, T80) were measured. Shown in Table 2 below.

Emission color at a luminance of 20,000 nits for OLEDs made in Device Examples 16 and 17 and Comparative Examples 14 and 15, and the time it took for the luminance to drop from 100% to 80% (lifetime, T80) ) are shown in Table 3 below.

From Tables 1-3 above, it can be seen that OLEDs containing specific combinations of compounds according to the present disclosure as host materials have comparable levels of drive voltage and/or luminous efficiency compared to OLEDs containing conventional compounds (comparative examples). can be seen to exhibit significantly improved life characteristics while having

In general, green-emitting organic electroluminescent devices have shorter lifetimes compared to red-emitting organic electroluminescent devices. To improve the lifetime properties of green-emitting organic electroluminescent devices, the present disclosure used compounds with deuterated moieties. Without being bound by theory per se, when an organic electroluminescent compound is substituted with deuterium, it lowers the zero-point vibrational energy of the compound and increases the bond dissociation energy (BDE) in the compound. It can increase the stability of the compound. It is understood that the application of deuterated moieties to the H-host can increase the stability of the H-host and reduce host degradation, thereby improving lifetime properties. FIG. 1 illustrates a graph showing the increase in bond dissociation energy associated with deuteration.

Device Examples 18-20: Fabrication of OLEDs Comprising Compounds According to the Present Disclosure as the Sole Host OLEDs were produced in the same way.

Comparative Examples 16 and 17: Fabrication of OLEDs Containing Comparative Compounds as Sole Hosts In the same manner as in Device Example 18, except only the hosts shown in Tables 4 and 5 below were used as hosts in the emissive layer. OLEDs were produced.

The emission color at a luminance of 20,000 nits and the time required for the luminance to drop from 100% to 80% (lifetime, T80) of the OLEDs produced in Device Examples 18 and 19 and Comparative Example 16 were reduced. shown in Table 4.

The emission color at a luminance of 20,000 nits and the time required for the luminance to drop from 100% to 80% (lifetime, T80) for the OLEDs produced in Device Example 20 and Comparative Example 17 are shown in the table below. 5.

From Tables 4 and 5 above, it can be seen that the organic electroluminescent compounds according to the present disclosure exhibit superior emission properties compared to conventional materials. In addition, OLEDs using compounds according to the present disclosure as host materials exhibit excellent emission properties as well as improved lifetime properties.

Device Examples 21 and 22: Fabrication of OLEDs Comprising Compounds According to the Disclosure as the Sole Host compound HT-4 was introduced into another cell of a vacuum evaporator and evaporated by applying an electric current to the cell, thereby forming a 60 nm thick layer on the first hole-transporting layer. A second hole-transport layer having a thickness was formed. A host compound shown in Table 6 below was introduced as a host into a cell of the vacuum evaporator, and compound D-39 was introduced as a dopant into another cell. The host material and the dopant material are evaporated at different rates, the dopant is evaporated with a doping amount of 3% by weight based on the total amount of the host and the dopant, and the light emitting layer has a thickness of 40 nm on the second hole transport layer. formed. Compound ET-1 and compound EI-1 as electron-transporting materials were evaporated at a weight ratio of 50:50 to form an electron-transporting layer with a thickness of 35 nm on the light-emitting layer.

Comparative Example 18 Preparation of an OLED Containing a Comparative Compound as the Sole Host An OLED was prepared in the same manner as in Device Example 21, except that only the host compounds shown in Table 6 below were used as the sole host in the emissive layer. manufactured.

Driving Voltage, Luminous Efficiency, and Color at 1,000 Nits Luminance of OLEDs Produced in Device Examples 21 and 22 and Comparative Example 18, and from 100% to 90% Luminance at 10,000 Nits Luminance The time required for degradation (lifetime, T90) is shown in Table 6 below.

Device Examples 23 and 24: Fabrication of OLEDs co-evaporated with a first host compound and a second host compound according to the present disclosure In the same manner as in Device Example 21, except that the emissive layer was formed as follows. OLEDs were prepared: a first host compound and compound H2-A (second host) shown in Table 7 below were introduced into two cells of a vacuum evaporator as hosts, and compound D-39 as a dopant in another introduced into the cell. The two host materials are evaporated in a ratio of 1:1, the dopant materials are evaporated simultaneously in different ratios, the dopant is evaporated with a doping amount of 3% by weight based on the total amount of the host and the dopant, and the second hole is A light-emitting layer with a thickness of 40 nm was formed on the transport layer.

Comparative Examples 19 and 20: Fabrication of OLEDs Containing Comparative Compounds as First Hosts In the same manner as in Device Example 23, except the compounds shown in Table 7 below were used as the first hosts in the emissive layer. OLEDs were produced.

Driving voltage, luminous efficiency, and emission color at 1,000 nits luminance of OLEDs fabricated in Device Examples 23 and 24 and Comparative Examples 19 and 20, and luminance from 100% to 80 at 10,000 nits luminance The time it took to drop to % (lifetime, T80) is shown in Table 7 below.

From Tables 6 and 7 above, it can be confirmed that the organic electroluminescent compounds according to the present disclosure exhibit superior emission properties compared to conventional materials. In addition, OLEDs comprising compounds according to the present disclosure, either as a single host or as one of multiple hosts, compared to OLEDs comprising conventional compounds while having comparable levels of driving voltage and/or luminous efficiency, significantly It can be seen to exhibit improved life properties.

The compounds used in Device Examples and Comparative Examples are shown in Table 8 below.

Claims (19)

Equation 1 below:

[In Formula 1,
X represents O, S or Se;
HAr represents substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen atom;
L represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene:
R ₁ and R ₂ each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or —SiR ₁₁ R ₁₂ R ₁₃ represent;
R ₁₁ to R ₁₃ each independently represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
a represents an integer of 1 to 4, b represents an integer of 1 to 3, wherein when each of a and b is an integer of 2 or more, each of R ₁ and each of R ₂ are the same or may be different]
and a first host material comprising a compound represented by the following formula 2:

[In formula 2,
A ₁ and A ₂ each independently represent substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;
X ₁₁ to X ₂₆ each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;
one of X ₁₅ to X ₁₈ and one of X ₁₉ to X ₂₂ are bonded to each other to form a single bond;
provided that at least one of X ₁₁ , X ₁₈ , X ₁₉ and X ₂₆ is deuterium]
A plurality of host materials including a second host material including a compound represented by HAr is substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxaly nyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted napthyridinyl, substituted or unsubstituted 2. The plurality of host materials of claim 1, which are substituted benzothienopyrimidinyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted pyridopyrazinyl. Formula 1 above is represented by Formula 1-1 below:

[In formula 1-1,
X, R ₁ , R ₂ , L, a and b are as defined in claim 1;
X' ₁ to X' ₃ each independently represent CR' or N, where R' represents hydrogen or deuterium, and at least two of X' ₁ to X' ₃ represent N ;
R ₃ and R ₄ each independently represent substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3-30 membered) heteroaryl]
The plurality of host materials of claim 1, represented by: The above formula 1-1 is represented by the following formulas 1-1-1 to 1-1-4:

[In formulas 1-1-1 to 1-1-4,
X, X' ₁ -X' ₃ , R ₁ -R ₄ , L, a, and b are as defined in claim 1]
4. The plurality of host materials of claim 3, represented by any one of The above formula 2 is represented by the following formulas 2-1 to 2-8:

[In formulas 2-1 to 2-8,
A ₁ , A ₂ , and X ₁₁ to X ₂₆ are as defined in claim 1]
The plurality of host materials of claim 1, represented by any one of A ₁ and A ₂ in Formula 2 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted is benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl; A plurality of host materials according to claim 1 . Said compounds represented by Formula 1 are the following compounds:

2. The plurality of host materials of claim 1, which is at least one selected from the group consisting of: Said compound represented by Formula 2 is the following compound:

At least one selected from the group consisting of
In the above compounds, Dn represents that n number of hydrogens have been replaced with deuterium, n is an integer from 1 to 50.
A plurality of host materials according to claim 1 . The substituents of said substituted alkyl, said substituted aryl, said substituted arylene, said substituted heteroaryl, said substituted heteroarylene, said substituted dibenzofuranyl, said substituted dibenzothiophenyl, and said substituted carbazolyl are each independently deuterium cyano; carboxyl; nitro; hydroxyl; unsubstituted or deuterium-substituted (C1-C30)alkyl; halo(C1-C30)alkyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; -C30)arylthio; unsubstituted or substituted with at least one of deuterium, (C1-C30)alkyl, (C6-C30)aryl, (3-50 membered)heteroaryl, and di(C6-C30)arylamino unsubstituted or deuterium, cyano, (C1-C30)alkyl, (3-30 membered)heteroaryl, mono- or di-(C6-C30)arylamino, and (C6-C30)aryl substituted with at least one tri(C6-C30)arylsilyl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6 -C30) arylsilyl; (C1-C30) alkyldi(C6-C30) arylsilyl; amino; mono- or di-(C1-C30) alkylamino; mono- or di-(C2-C30) alkenylamino; mono- or di-(C6-C30)arylamino; mono- or di-(3-30 membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30) (C1-C30)alkyl(3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30membered)heteroarylamino; (C6-C30) aryl(3-30 membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di(C6-C30) arylbornyl; Di(C1-C30) alkyl (C1-C30)alkyl(C6-C30)arylbornyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl 3. The plurality of host materials of claim 1, being at least one. An organic electroluminescent device comprising an anode, a cathode, and at least one emissive layer between the anode and the cathode, wherein at least one of the emissive layers comprises a plurality of host materials according to claim 1. containing device. Formula 1-A below:

An organic electroluminescent compound represented by
In formula 1-A,
X _a represents O or S;
R ₄₁ to R ₄₈ are each independently hydrogen, deuterium, or unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl (C6-C18 ) aryl or represented by formula 1-a below, provided that at least one of R ₄₁ to R ₄₈ is represented by formula 1-a below:

[In formula 1-a,
Ra-Rd are each independently hydrogen, deuterium, or (C6-C18)aryl unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl represents;
Ar _a and Ar _b are each independently unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterated terphenyl, unsubstituted or deuterated carbazolyl, unsubstituted or deuterated dibenzofuranyl, unsubstituted or deuterated dibenzothiophenyl , or combinations thereof, with the proviso that at least one of Ar _a and Ar _b comprises a substituted or unsubstituted carbazonyl]
A compound provided that it is represented by At least one of Ar _a and Ar _b in formula 1-a has the following formula 1-b1 or 1-b2:

(In formulas 1-b1 and 1-b2,
La is a single bond, unsubstituted or deuterated phenylene, unsubstituted or deuterated naphthylene, unsubstituted or deuterated biphenylene, or unsubstituted or deuterated representing a substituted terphenylene;
R ₅₁ to R ₅₉ are each independently hydrogen, deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or combinations thereof)
12. The organic electroluminescent compound according to claim 11, represented by The compounds represented by Formula 1-A are the following compounds:

12. The organic electroluminescent compound of claim 11, selected from the group consisting of: An organic electroluminescent material comprising an organic electroluminescent compound according to claim 11 . An organic electroluminescent device comprising the organic electroluminescent compound of claim 11 . Formula 1-B below:

[In formula 1-B,
X _a represents O or S;
R ₄₁ to R ₄₈ are each independently hydrogen; deuterium; unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl and (C6-C18)aryl (C6-C18) aryl; or -L _b -HAr _b , with the proviso that at least one of R ₄₁ -R ₄₈ represents -L _b -HAr _b ;
L _b represents unsubstituted or deuterium-substituted naphthylene;
HAr _b has the following formula 1-b:

(In formula 1-b,
Ar _a and Ar _b are each independently unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterated terphenyl, unsubstituted or deuterated carbazolyl, unsubstituted or deuterated dibenzofuranyl, unsubstituted or deuterated dibenzothiophenyl , or combinations thereof, wherein at least one of Ar _a and Ar _b is carbazolyl unsubstituted or substituted with at least one of deuterium and (C6-C18)aryl, unsubstituted or deuterium or dibenzothiophenyl unsubstituted or substituted with deuterium)
represented by]
An organic electroluminescent compound represented by. The compounds represented by Formula 1-B are the following compounds:

17. The organic electroluminescent compound of claim 16, selected from the group consisting of: 17. An organic electroluminescent material comprising the organic electroluminescent compound of claim 16. 17. An organic electroluminescent device comprising the organic electroluminescent compound of claim 16.

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